40983-94-6

Usage

Uses

Used in the Synthesis of Complex Carbohydrates:
Benzyl 4,6-O-benzylidene-alpha-D-mannopyranoside is used as a key intermediate in the synthesis of O-D-xylosyl-D-mannoses and their derivatives. These complex carbohydrates have significant applications in various fields, including pharmaceuticals, biochemistry, and materials science, due to their unique structural and functional properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzyl 4,6-O-benzylidene-alpha-D-mannopyranoside is used as a building block for the development of novel drug candidates targeting various diseases. Its unique structure allows for the creation of glycoconjugates with specific biological activities, potentially leading to the discovery of new therapeutic agents.
Used in Biochemical Research:
Benzyl 4,6-O-benzylidene-alpha-D-mannopyranoside is also utilized in biochemical research as a valuable tool for studying the interactions between carbohydrates and proteins, as well as for understanding the role of glycosylation in various biological processes. Its unique structure enables researchers to probe the specificity and mechanisms of carbohydrate-binding proteins and enzymes.
Used in Materials Science:
In the field of materials science, Benzyl 4,6-O-benzylidene-alpha-D-mannopyranoside can be employed in the development of advanced materials with tailored properties. Its ability to form complex carbohydrates and glycoconjugates can be harnessed to create materials with specific recognition, binding, or self-assembly properties, which can be applied in areas such as sensors, drug delivery systems, and biocompatible coatings.

InChI:InChI=1/C20H22O6/c21-16-17(22)20(23-11-13-7-3-1-4-8-13)25-15-12-24-19(26-18(15)16)14-9-5-2-6-10-14/h1-10,15-22H,11-12H2/t15?,16-,17?,18-,19?,20-/m1/s1

Upstream product

• 4304-12-5 (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 83050-00-4 benzyl 2-O-acetyl-4,6-O-benzylidene-3-O-tosyl-β-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 83-87-4 D-glucose pentaacetate 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 2280-44-6 D-Glucose 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 530-26-7 D-Mannose 
• 7296-15-3 alpha-D-mannopyranoside 
• 25320-99-4 benzyl α-D-glucopyranoside 

Downstream Products

• 22893-77-2 benzyl-[O²,O³-diacetyl-O⁴,O⁶-((R)-benzylidene)-β-D-glucopyranoside] 
• 130610-56-9 benzyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 130610-63-8 benzyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 70144-60-4 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 86420-81-7 benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 130610-58-1 benzyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 130610-57-0 benzyl 3-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 83049-97-2 benzyl 4,6-O-benzylidene-2,3-di-O-ethyl-β-D-glucopyranoside 
• 82122-45-0 benzyl 4,6-O-benzylidene-2,3-di-O-propyl-β-D-glucopyranoside 
• 177567-39-4 benzyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-glucopyranoside 
• 183953-29-9 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 259826-53-4 benzyl 4,6-O-benzylidene-2,3-di-O-benzoyl-β-D-glucopyranoside 
• 67831-41-8 benzyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 83050-03-7 benzyl 4-O-benzyl-3-deoxy-2-O-methyl-β-D-ribo-hexopyranoside 

Relevant academic research and scientific papers

Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har

Synthesis of Bradyrhizose from d -Glucose

We describe the synthesis of the unusual bicyclic sugar bradyrhizose in 14 steps and a 6% overall yield from d-glucose. The synthesis involves the elaboration of a trans-fused carbocyclic ring onto the preexisting glucopyranose framework followed by adjus

Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae

The incidences of primary, pyrogenic liver abscess complicated by meningitis and septic endophthalmitis caused by Klebsiella pneumoniae has increased globally. Earlier studies have shown that the capsular polysaccharide (CPS) of Klebsiella pneumoniae plays an important role in the resistance to phagocytosis and related pathogenicity. The first chemical synthesis of the trisaccharide repeating unit of this CPS has been achieved via stereoselective glycosylation with orthogonal and appropriate protecting groups. A new method for the pyruvylation of trans diol was developed.

INHIBITORS OF HEXOKINASE AND METHODS OF USE THEREOF

Provided herein are substituted substituted heterocycles useful as inhibitors of the HKII enzyme. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention further provides medical uses of substituted heterocycles, for example, as antitumor agents.

Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo

Glycoconjugation is a promising strategy for specific targeting of cancer. In this study, we investigated the effect of d-glucose substitution position on the biological activity of glucose-platinum conjugates (Glc-Pts). We synthesized and characterized all possible positional isomers (C1α, C1β, C2, C3, C4, and C6) of a Glc-Pt. The synthetic routes presented here could, in principle, be extended to prepare glucose conjugates with different active ingredients, other than platinum. The biological activities of the compounds were evaluated both in vitro and in vivo. We discovered that varying the position of substitution of d-glucose alters not only the cellular uptake and cytotoxicity profile but also the GLUT1 specificity of resulting glycoconjugates, where GLUT1 is glucose transporter 1. The C1α- and C2-substituted Glc-Pts (1α and 2) accumulate in cancer cells most efficiently compared to the others, whereas the C3-Glc-Pt (3) is taken up least efficiently. Compounds 1α and 2 are more potent compared to 3 in DU145 cells. The α- and β-anomers of the C1-Glc-Pt also differ significantly in their cellular uptake and activity profiles. No significant differences in uptake of the Glc-Pts were observed in non-cancerous RWPE2 cells. The GLUT1 specificity of the Glc-Pts was evaluated by determining the cellular uptake in the absence and in the presence of the GLUT1 inhibitor cytochalasin B, and by comparing their anticancer activity in DU145 cells and a GLUT1 knockdown cell line. The results reveal that C2-substituted Glc-Pt 2 has the highest GLUT1-specific internalization, which also reflects the best cancer-targeting ability. In a syngeneic breast cancer mouse model overexpressing GLUT1, compound 2 showed antitumor efficacy and selective uptake in tumors with no observable toxicity. This study thus reveals the synthesis of all positional isomers of d-glucose substitution for platinum warheads with detailed glycotargeting characterization in cancer.

TANNIN INHIBITORS OF HIV

The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.

Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity

A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cel

Glycosylation using 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose, - galactose, and -mannose with the aid of p-nitrobenzenesulfonyl chloride- silver trifluoromethanesulfonate-triethylamine system

This report describes a simple synthesis of 2-azido-3,4,6-tri-O-benzyl- 2-deoxy-D-glucopyranose. Glycosylation using this as well as 2-azido-3,4,6- tri-O-benzyl-2-deoxy-D-galactopyranose and -mannopyranose was achieved with the aid of a reagent system consisting of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, and its modifications. O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-(1 → 4)-O-α-D-mannopyranosyl- (1 → 4)-a-D-mannopyranose, the repeating unit of the main chain of the O- specific cell wall polysaccharide of E. coli 058 was synthesized.

An efficient method for the synthesis of a 1,6-anhydro-α-D-galactofuranose derivative and its application in the synthesis of oligosaccharides

Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-β-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactofuranoside (1). The anhydro compound 3 was converted to the

Prespacer Glycosides in Glycoconjugate Chemistry. Dibromoisobutyl Glycosides for the Synthesis of Neoglycolipids, Neoglycoproteins, Neoglycparticles, and Soluble Glycosides

3-Bromo-2-(bromomethyl)propyl (dibromoisobutyl or DIB) mono- to tetrasaccharide glycosides were prepared in moderate to high yields by treatment of the corresponding 1-O-acetyl saccharides with 3-bromo-2-(bromomethyl)propanol (DIBOL) and boron trifluoride